Trifluoroacetic acid → Trifluoroacetic acid

Participants

Role	Name	HCID	Charge
Reactant	Trifluoroacetic acid	HCID 6422	—
Reactant	Sodium Hydroxide	HCID 14798	—
Reactant	N-(tert-Butyl)thiourea	HCID 737374	—
Reactant	Methyl 2-(2-bromo-ethanoyl)-3-cyclohexyl-1-(2-morpholin-4yl-2-oxo-ethyl)-1H-indole-6carboxylate	HCID 21105283	—
Solvent	Dimethyl Sulfoxide	HCID 679	—
Product	Trifluoroacetic acid	HCID 6422	—
Product	2-(2-Tert-butylamino-thiazol-4-yl)-3-cyclohexyl-1-(2-morpholin-4-yl-2-oxo-ethyl)-1h-indole-6-carboxylic acid	HCID 21105252	—

Reaction Steps

The bromomethylketone of example 11 (39.6 mg, 0.078 mmol, 1 equiv.) was dissolved in DMSO (1 mL) and N-tertbutylthiourea (12.4 mg, 0.094 mmol, 1.2 equiv.) was added. The mixture was stirred for 2 h at room temperature. 10 N NaOH (24 μL) was added and after stirring for 4 h at room temperature, another portion of 10 N NaOH (24 μL) was added and the mixture stirred 24 h at room temperature to complete the hydrolysis. The reaction mixture was then neutralized by addition of TFA and the title product of example 12 isolated directly from the reaction mixture by preparative HPLC as a white amorphous TFA salt (21 mg).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US07888363B2
Source dataset	uspto-grants-2011_02
ORD ID	ord-9927000c0d364b42b1a3ff6f8941cd86
Source note	uspto-grants-2011_02